DD143251A5 - Verfahren zur herstellung von phenylnitraminverbindungen - Google Patents

Verfahren zur herstellung von phenylnitraminverbindungen Download PDF

Info

Publication number: DD143251A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; plants; alkyl; formula; solution
Prior art date: 1978-02-21

Application number

DD79211101A

Other languages

German (de)

English (en)

Inventor

Barrington Cross

David H Dawe

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-02-21

Filing date

1979-02-19

Publication date

1980-08-13

1979-02-19 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1980-08-13 Publication of DD143251A5 publication Critical patent/DD143251A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 37
238000004519 manufacturing process Methods 0.000 title description 5
239000000460 chlorine Substances 0.000 claims description 153
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
241000196324 Embryophyta Species 0.000 description 40
239000000243 solution Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
201000010099 disease Diseases 0.000 description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
150000003839 salts Chemical class 0.000 description 19
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
-1 IV Chemical class 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
231100000674 Phytotoxicity Toxicity 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
230000000855 fungicidal effect Effects 0.000 description 11
125000001309 chloro group Chemical group Cl* 0.000 description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
244000141359 Malus pumila Species 0.000 description 7
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239000012141 concentrate Substances 0.000 description 7
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238000011156 evaluation Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
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235000011430 Malus pumila Nutrition 0.000 description 6
206010037888 Rash pustular Diseases 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
150000001448 anilines Chemical class 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
AHSTZDNKAGCTKO-UHFFFAOYSA-N n-(2,3,5,6-tetrachlorophenyl)nitramide Chemical compound [O-][N+](=O)NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl AHSTZDNKAGCTKO-UHFFFAOYSA-N 0.000 description 6
208000029561 pustule Diseases 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
240000005979 Hordeum vulgare Species 0.000 description 5
235000007340 Hordeum vulgare Nutrition 0.000 description 5
235000015103 Malus silvestris Nutrition 0.000 description 5
241001337928 Podosphaera leucotricha Species 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
206010061217 Infestation Diseases 0.000 description 4
241001330975 Magnaporthe oryzae Species 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
241000228452 Venturia inaequalis Species 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000005507 spraying Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000012085 test solution Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 3
241001480061 Blumeria graminis Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 3
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
159000000009 barium salts Chemical class 0.000 description 3
239000000428 dust Substances 0.000 description 3
230000002538 fungal effect Effects 0.000 description 3
244000053095 fungal pathogen Species 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
238000006396 nitration reaction Methods 0.000 description 3
229960003531 phenolsulfonphthalein Drugs 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
235000001674 Agaricus brunnescens Nutrition 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 2
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
125000003047 N-acetyl group Chemical group 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
241001123569 Puccinia recondita Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
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239000002270 dispersing agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
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235000013399 edible fruits Nutrition 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
IDNUEBSJWINEMI-UHFFFAOYSA-N ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
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150000004692 metal hydroxides Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
235000016709 nutrition Nutrition 0.000 description 2
244000052769 pathogen Species 0.000 description 2
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239000003415 peat Substances 0.000 description 2
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239000011591 potassium Substances 0.000 description 2
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WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
238000005979 thermal decomposition reaction Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
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238000010956 selective crystallization Methods 0.000 description 1
210000000582 semen Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD79211101A 1978-02-21 1979-02-19 Verfahren zur herstellung von phenylnitraminverbindungen DD143251A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/879,340 US4130645A (en)	1978-02-21	1978-02-21	Fungicidal phenylnitramines and new phenylnitramines

Publications (1)

Publication Number	Publication Date
DD143251A5 true DD143251A5 (de)	1980-08-13

Family

ID=25373944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79211101A DD143251A5 (de)	1978-02-21	1979-02-19	Verfahren zur herstellung von phenylnitraminverbindungen

Country Status (8)

Country	Link
US (1)	US4130645A (da)
EP (1)	EP0003881A1 (da)
JP (1)	JPS54122233A (da)
AU (1)	AU4408279A (da)
BR (1)	BR7900812A (da)
DD (1)	DD143251A5 (da)
DE (1)	DE2902890A1 (da)
DK (1)	DK72979A (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4367339A (en) *	1980-08-18	1983-01-04	American Cyanamid Company	Substituted N-nitroaniline compounds and inorganic and organic salts thereof useful for enhancing auxiliary branching, canopy flowering and crop yield of plant and as lodging inhibitors therefor
IL62004A0 (en) *	1980-02-19	1981-02-27	American Cyanamid Co	Method for the control of stem growth and stem stiffness of selected crops
EP0059226A1 (en) *	1981-01-24	1982-09-08	American Cyanamid Company	Substituted N-nitroaniline compounds and inorganic and organic salts thereof useful for improving crop yields
US4643755A (en) *	1981-02-19	1987-02-17	American Cyanamid Company	Method for the control of stem growth and stem stiffness of graminaceous crops
CN102311361B (zh) *	2011-09-08	2014-02-26	华中农业大学	化合物n-硝基-2,4,6-三氟苯胺及其合成方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB430236A (en) *	1933-12-12	1935-06-12	Marcel Joseph Gustave Bader	Compositions for the production of azo dyestuffs
US3249496A (en) *	1965-06-14	1966-05-03	Monsanto Co	Soil fungicide
US3844762A (en) *	1971-05-11	1974-10-29	American Cyanamid Co	Phenylnitramine herbicides
GB1329012A (en) *	1971-07-20	1973-09-05	Monsanto Chemicals	Trifluoromethylnitraminobenzenes and herbicidal compositions containing them

1978
- 1978-02-21 US US05/879,340 patent/US4130645A/en not_active Expired - Lifetime
1979
- 1979-01-25 DE DE19792902890 patent/DE2902890A1/de not_active Withdrawn
- 1979-02-08 AU AU44082/79A patent/AU4408279A/en not_active Abandoned
- 1979-02-09 BR BR7900812A patent/BR7900812A/pt unknown
- 1979-02-09 EP EP79300201A patent/EP0003881A1/en not_active Withdrawn
- 1979-02-19 DD DD79211101A patent/DD143251A5/de unknown
- 1979-02-20 DK DK72979A patent/DK72979A/da unknown
- 1979-02-21 JP JP1961679A patent/JPS54122233A/ja active Pending

Also Published As

Publication number	Publication date
US4130645A (en)	1978-12-19
AU4408279A (en)	1979-08-30
EP0003881A1 (en)	1979-09-05
BR7900812A (pt)	1979-09-04
DK72979A (da)	1979-08-22
JPS54122233A (en)	1979-09-21
DE2902890A1 (de)	1979-08-23

Publication	Publication Date	Title
DE2661042C2 (da)	1989-11-09
EP0482410A2 (de)	1992-04-29	Antimikrobielle Mittel sowie substituierte 2-Cyclohexan-1-yl-amin-Derivate und deren Herstellung
CH603041A5 (en)	1978-08-15	N-Furoyl-N-aryl-alanine esters
DE3740840A1 (de)	1989-06-08	2,2-difluorcyclopropylethanderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
EP0137868B1 (de)	1987-08-12	1-Substituierte Imidazol-5-carbonsäurederivate, ihre Herstellung sowie ihre Verwendung als Biozide
DD297641A5 (de)	1992-01-16	N-phenylpyrazolderivate, ihre herstellung und ihre verwendung als pesticide
DE2513730C2 (de)	1987-02-12	N-(1'-Methoxycarbonyl-äthyl)-N-halogenacetyl-2-halogenaniline, Verfahren zu deren Herstellung und diese Verbindungen enthaltende fungizide Mittel
DE2643477A1 (de)	1977-04-07	Mikrobizide
EP0206004A1 (de)	1986-12-30	E-Isomere von N alpha-(2-Cyan-2-alkoximino-acetyl)-amino-säurederivaten und -peptiden
DE2905650C2 (da)	1989-02-16
DE2832234A1 (de)	1980-01-31	Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2600799A1 (de)	1977-07-14	Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE1955750A1 (de)	1971-05-13	Ureidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung
DD143251A5 (de)	1980-08-13	Verfahren zur herstellung von phenylnitraminverbindungen
DE2812662C2 (da)	1990-02-15
DE2951164A1 (de)	1981-07-16	Substituierte triazolylmethyl-tert.-butyl-ketone, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte
DE2525855C3 (de)	1978-06-22	Substituierte Benzoesäureanilide sowie ein diese Verbindungen enthaltendes Mittel
DE2813335C2 (de)	1987-04-09	N-acylierte N-Alkylaniline, Verfahren zu ihrer Herstellung sowie mikrobizide Mittel enthaltend diese als Wirkstoffe
PL154259B1 (en)	1991-07-31	Pesticide containing novel derivatives of 2-phenylimidazole
DD142278A5 (de)	1980-06-18	Mikrobizides mittel
DE3145846A1 (de)	1983-05-26	Cycloalkyl-((alpha)-triazolyl-ss-hydroxy)-ketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren
DD157292A5 (de)	1982-11-03	Mittel zur behandlung von pilzinfektionen
DE2919825C2 (da)	1988-09-01
EP0288493B1 (de)	1991-05-29	3-halogensuccinimide
DE2604761A1 (de)	1977-08-11	Acylierte imidazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide